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Umpolung reactivity in amide and peptide synthesis

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Shen, Bo, Makley, Dawn M., Johnston, Jeffrey N.·2010·Nature

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Abstract

The amide bond is one of nature's most common functional and structural elements, as the backbones of all natural peptides and proteins are composed of amide bonds. Amides are also present in many therapeutic small molecules. The construction of amide bonds using available methods relies principally on dehydrative approaches, although oxidative and radical-based methods are representative alternatives. In nearly every example, carbon and nitrogen bear electrophilic and nucleophilic character, respectively, during the carbon-nitrogen bond-forming step. Here we show that activation of amines and nitroalkanes with an electrophilic iodine source can lead directly to amide products. Preliminary observations support a mechanism in which the polarities of the two reactants are reversed (German, umpolung) during carbon-nitrogen bond formation relative to traditional approaches. The use of nitroalkanes as acyl anion equivalents provides a conceptually innovative approach to amide and peptide synthesis, and one that might ultimately provide for efficient peptide synthesis that is fully reliant on enantioselective methods.

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Authors: Shen, B., Makley, D. M., & Johnston, J. N.
Affiliations: Vanderbilt University (US)
Corresponding author: Johnston, Jeffrey N.
ORCID: Johnston, Jeffrey N.
Venue: Nature
Publisher: Springer Science and Business Media LLC
Published: 2010-06
Volume: 465
Issue: 7301
Pages: 1027-1032
ISSN: 0028-0836 (ISSN-L)
1476-4687
DOI: 10.1038/nature09125
PMC: PMC2945247
OpenAlex: W2094137451
Cited by: 318
References: 48
Citations by year: 2026: 8 · 2025: 21 · 2024: 13 · 2023: 10 · 2022: 11 · 2021: 13 · 2020: 14 · 2019: 14 · 2018: 23 · 2017: 23 · 2016: 25 · 2015: 33 · 2014: 28 · 2013: 21 · 2012: 30
FWCI: 10.56
Type: journal article
Language: en
Open access: green
www.ncbi.nlm.nih.gov
Licence: www.springer.com/tdm (tdm)
Locations: Nature (publishedVersion)
PubMed (publishedVersion)
Europe PMC (PubMed Central) (acceptedVersion)
PubMed Central (acceptedVersion)
RePEc: Research Papers in Economics (submittedVersion)
Funders: Vanderbilt University
National Institute of General Medical Sciences (T32GM065086, R01GM063557, GM084333, R01GM084333)
Topics: Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Analysis
Physical Sciences › Chemistry › Organic Chemistry › Advanced Synthetic Organic Chemistry
Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
Keywords: umpolung, amide synthesis, peptide synthesis, nitroalkanes, amines, acyl anion equivalents, asymmetric synthesis, C–N bond formation
MeSH terms: Alkanes, Amides, Amines, Carbon, Ethane, Glycine, Models, Chemical, Nitro Compounds, Nitrogen, Peptides

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Umpolung reactivity in amide and peptide synthesis

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